We want to help plan and organize everyone's life while providing a solid foundation for personal and financial growth.

About us

You have more stuff than you think. It can be daunting to organize all your financial documents, assets, identity and important everyday life documents. Thinking about how to securely store and share your information, track who it is shared with, and trying to gather and manage all your information from so many sources, anyone would feel overwhelmed. SideDrawer is here to help.
SideDrawer is a secure and real-time Life Planning and Organization platform that allows you to easily organize and share your personal and family information and important contacts -from any device- including banking, investments, identity, real estate and all other critical information. SideDrawer offers guided organization, and the flexibility to provide as much or as little information as you like. With a user-friendly interface, and permission-based settings, you can invite collaborators to help you with your documents allowing easy access to your trusted advisors and loved ones.
You will be able to identify your key contacts linked to your important records, such as your advisors (i.e.: lawyer, accountant, investment advisor, insurance broker, executor, etc.) so people with access to your SideDrawer will always know who to contact in each and every case.

Our story


With the understanding of a much greater need, we completely redesigned and redeveloped our collaborative online and mobile platform as a Life Planning and Organization Platform for all stages of your life!


SideDrawer v1.0 was released into the app store for iOS and Android. We received great feedback and adoption, which helped us realize an unmet need for an ongoing tool/platform like this in every household and with EVERY individual. Not only is there a need for storing pertinent documents in case of an emergency, but also for all aspects of life -from passwords, to cable bills, to properties- we need help planning and organizing our entire life, not just the end.


The concept of SideDrawer was conceived through a simple, yet impactful thought of "would my family know where all of my critical documents were if something were to happen to me?". This statement resonates with each and every individual, and we wanted to solve that problem!

Our team

SideDrawer's team is comprised of individuals with extensive and diverse backgrounds.

J. Gaston Siri

J. Gaston Siri
Chief Executive Officer - Co-Founder

Gaston was most recently CTO at Flexiti Financial (a Globalive business) that originated over $300M of Point of Sale Consumer financing.

Gaston led the team that designed, developed and launched Flexiti's home-grown credit card platform and consumer applications. One of his most recent achievements was the migration of TD's $250M private label credit card portfolio (back book & forward flow) into Flexiti's ecosystem.

Gaston built the technology team from the ground up.

Prior to Flexiti, Gaston founded several businesses that have been sold or are currently operating with their own management team.

Jamie Wolkove

Jamie Wolkove
VP of Marketing and Sales

Jamie is a business development-oriented entrepreneur who founded his own digital marketing agency, which continues to operate today with its own management team.

Jamie has led and contributed to the development of cross-border sales teams.

Jamie was most recently with ClearBlue Technologies Group where he drove material new business, identified and created new sales channels, generated significant revenue that was more than 150% above target and well ahead of timing.

Marc Milgrom

Marc Milgrom
Chief Strategist

Marc is an emerging technology executive with strengths in strategy, leadership and execution, including domestic and international experience in operations, business transformation and product development.

Marc's experience includes building and selling an early stage SaaS company as President and CEO of Filemobile. Prior to that, Marc was a tax partner at PricewaterhouseCoopers (PwC) and a member of PwC's Leadership Team that managed its Canadian affiliate firm. Management responsibilities included the firm's market facing industry program, sales and business development, knowledge management and digital transformation initiatives.

Marc holds a Doctor of Jurisprudence from the University of Toronto. Previous community involvement roles include being a member of the Board of Trustees' Research Committee of University Health Network and Chair of the Board of Directors of the Arthritis Research Foundation.

Marcos Tardini

Marcos Tardini
Director IT Infrastructure

Marcos has more than 14 years of expertise in IT having worked for global companies including IBM, Globant, TCS and Flexiti Financial.

He has broad experience in corporate IT infrastructure, within a variety of industries such as Telecommunications, Banking, Retail and Financial Services.

Marcos is a natural leader with the ability to drive IT teams to successfully implement digital and infrastructure transformation initiatives.

Over the last 5 years, he’s been implementing continuous integration of IT services, including Docker, Kubernetes and Terraform among others.

With Gaston, Marcos led the hardening of Flexiti's infrastructure, taking the company's processes and policies to a global-market-ready status.

His previous experience includes working for large and medium sized corporations in the USA, India and Latin America.

Brittany Allison

Brittany Allison
Customer Success Manager

Brittany has over 15 years of customer service experience, and recently was a project coordinator at Clear Blue Technologies alongside Jamie.

She managed, budgeted and completed multiple ongoing projects each upwards of $350K, while maintaining all client communications. Brittany was responsible for maintaining all current and potential customer relationships in good standing.

Given her customer relationship experience, she will be leading SideDrawer's Customer Success Team.

She holds an advance diploma with honours in Marketing from George Brown College.

Our board members

J. Gaston Siri

J. Gaston Siri - Co-Founder & CEO

Gaston founded several businesses that have been sold or are currently operating with their own management team.

Gaston has been an entrepreneur his entire life, having successfully navigated through several economic crises in his career.

Ray Sharma

Ray Sharma - Founding Partner & CEO of Extreme Venture Partners

Ray is the founder and CEO of Extreme Venture Partners, one of Canada's top seed stage venture fund.

Ray and Extreme Venture Partners has lead funded or founded 100+ startups with a world-class track record in seed investments including exits to Apple, Google, Electronic Arts, McKesson, Salesforce and others. In addition, Ray has founded Xtreme Labs (Canada's largest mobile app developer at time of acquisition;) Extreme Innovations, (acquired) a startup that created startups; Extreme Accelerator, a next-gen accelerator with a focus on bringing international startups to Toronto. Other notable startups that Ray has co-founded includes Thinkdata, Hackworks, XMG Studio, and Hackergal.

Previously Ray spent 10 years on Bay Street & Wall Street in investment banking research. During that period Ray was the top-ranked wireless technology analyst based on Greenwich and Brendan Woods International surveys of fund managers for 5 of 8 eligible years.

Ray's community service includes the Ontario Judicial Council; Royal Ontario Museum Board of Trustees; Treasury Board of Canada Advisory Board; founder and leader of national hackathon competitions Great Canadian Appathon, Canadian Open Data Experience (CODE), and Hackergal. Hackergal is the organizer of the largest Hackathon ever held in Canada.

Our advisors

Matias Siri

Matias Siri

Matias is a professional in the Information Technology field with over 20 years of experience and specifically over 15 years of experience in the Information Security field. Matias serves as the Cyber Security Engineering Manager at the OCC and oversees deploying and maintaining all Cyber Security platforms that secure and protect the Agency's networks and assets. Prior to joining the OCC, Matias served as Security Engineering Branch Chief at the Executive Office of the President supporting the White House, OMB, the Office of the Vice President, and the additional EOP components.

Matias holds master's degree in Information Security and Assurance from George Mason University. Matias also holds the Certified Information Systems Security Professional (CISSP) certification from ISC.

Sam Sivarajan

Sam Sivarajan

Sam has over 25 years of international experience in investment banking and investment management. Prior to joining Crosbie, Sam held senior leadership roles in wealth management at top Canadian and global firms. In these roles, he was an intrapreneur building acclaimed investment businesses and leading professional teams to help clients meet their business and financial objectives.

Sam spent many years in Europe where he held progressively senior roles in investment banking with some of the largest global firms. Sam played key roles in providing strategic advice, executing on buy and sell side mandates and in raising private and public capital. Sam's clients included well-known private and public companies, boards of directors, as well as government stakeholders.

Sam has completed his doctorate from the University of Manchester, where his thesis was on investor decision-making. He also has a law and MBA degrees from the University of Toronto and a degree in Economics from Western University.

Kavina Nagrani

Kavina Nagrani, J.D, TEP, HBA

After spending the first years of her legal career in private practice for two top-tier law firms, Kavina founded NIKA LAW LLP, a boutique Wills, Estates & Elder Law firm in the Etobicoke/Mississauga border.

Pre-law, Kavina was a Director in the Information Technology space, managing and consulting on multi-million dollar software implementation initiatives across Canada, the USA and in Mexico.

She was also an instrumental advisor to the Canadian channel of Just-Eat.ca (now Skipthedishes) before its public offering and offers advisory support to other local technology companies and initiatives.

As an estate planning lawyer herself, Kavina's real-life experience with her clients has been invaluable to developing the Sidedrawer professional user experience and our collaboration models.

Thomas Johnston

Thomas Johnston

Tom was most recently President of CI Institutional, a $17B book of business within CI Financial (CIX.TO on TSX).

Tom was previously Head of Canada & CEO at UBS Global Asset Management (UBS Canada).

Tom's role identifying strategic partners and leveraging his relationships are crucial for the expanding and deploying of SideDrawer.

Ron Schwarz

Ron Schwarz

Ron is an independent investor, corporate director and capital markets professional with 25 years of industry experience.

Ron was a Managing Director and Head of Canadian Cash Equities at CIBC Wholesale Bank. He was responsible for equity sales, trading, research, prime brokerage and electronic trading operations.

Mr. Schwarz graduated from Concordia University and is a CFA charterholder.

Work with us

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See all available positions and get started with your SideDrawer career TODAY!